I'm Anne. I've been preparing taxes for 27 years and I'll be happy to help you.
The answer to your question depends on the type of investment distribution you're looking at.
If you're looking at a 1099R from a Roth IRA, then that box should have the tax payer's contributions to the Roth.
If you're looking at a 1099R from a pension , that box could contain either the tax payer's investment into the pension, OR that box also reports the $ amount of medical insurance the tax payer paid.
You will need to ask the tax payer if they know what that box represents. If they do not know, then you will have to have the taxpayer contact the company that holds the pension, and ask them what that $ amount is.
Most tax payers know, especially if it is their medical insurance , what the $ amount in that box represents.
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